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Expert guide to Tuscany

Tuscany’s second city rivals Florence for Renaissance palazzi and art treasures – go now to enjoy its balmy autumn and fewer visitors, says Tim Jepson.

Siena takes some beating. In the Campo, its central piazza, it possesses Europe’s finest medieval square, scene of the Palio horse race, Italy’s most dramatic historical spectacle. Its cathedral is central Italy’s most beautiful, and the art in the many churches, galleries and museums would keep you busy for weeks.

Above all, though, the city is an intimate and civilised place – a place alla misura dell’uomo, or “made to the measure of man”, as the Italians have it – and its sleepy, honey-stoned streets are in marked medieval contrast to the more gaunt and impersonal grandeur of Florence’s Renaissance heart.

While never as overrun as Florence, Siena sees plenty of visitors, but by October and November, the Sienese are reclaiming their streets, and the enervating heat has given way to the balmy, gentle warmth of the Tuscan autumn.

Food in the restaurants sees the arrival of seasonal specialities such as porcini (cep), plump grapes from Puglia, and the first winter truffles. Tuscany’s best wine, from Montalcino and Montepulciano to the south, and Bolgheri to the west, is available year-round.

Mid-range: On the edge of the old city but within an easy walk of the sights, the 39-room Palazzo Ravizza (Pian dei Mantellini 34; 0039 577 280462; palazzoravizza.it) has been run by the same family since 1924, and cultivates the air of an elegant private home. Front-facing rooms are larger, but the rear, garden-view rooms are more romantic. Double B&B from £73.

On a budget: The Tre Donzelle (Vicolo Donzelle, off Via Cecco Angiolieri; 0039 577 280358; tredonzelle.com) is basic, but its prices, and position seconds from the Campo, mean you must book well in advance. If you arrive to find it full, try the two-star Piccolo Hotel Etruria (0039 577 288088; hoteletruria.com) a few doors down and £20 more expensive. Doubles from £48, room only.

On arrival

Have an aperitif on the Campo. All the bars offer the same beautiful prospect, but locals favour Bar Il Palio (Piazza del Campo 47; 0039 577 282055). Food on the Campo is unexceptional – overpriced pizza everywhere – the setting is the trade-off. Or walk a few moments to the tiny Il Carroccio (Via Casato di Sotto 32; 0039 577 41165; closed Monday; mains from £5.60), a simple, Slow Food-endorsed trattoria.

Day one

9am

It’s tempting to start where you left off and head to the Campo for a cappuccino. Resist: you’ll be back there soon enough. Instead, make for Piazza Salimbeni, at the northern end of Banchi di Sopra, Siena’s main artery.

Interlocking palaces flank the piazza: the Spannocchi was Siena’s first Renaissance palazzo (1473), while the earlier Salimbeni is a Gothic final flourish housing the Monte dei Paschi, founded in 1472, and the world’s oldest surviving bank.

Walk south down shop-lined Banchi di Sopra, noting the fortress-like 13th-century Palazzo Tolomei on the right. Turn right to take Via delle Terme (site of the Roman baths, or terme) and Via di Diacceto to emerge in Piazza San Giovanni, behind the Duomo, or cathedral. Don’t take the left-hand steps, but follow Via dei Fusari right for a more dramatic view of the cathedral’s majestic façade.

10am

Admire the exterior of the Duomo (Piazza del Duomo; 0039 577 286300; operaduomo.siena.it; £2.40 or included in the price of an Opa Si Pass, £9.60; see below) and the remnants of a second, larger cathedral abandoned after the Black Death of 1348, which reduced Siena’s population from 100,000 to 30,000. Had it been completed, this would have been Italy’s largest cathedral, deliberately far larger than that of Florence.

Ahead is the ticket office for the Museo dell’Opera. Buy the Opa Si Pass here: it includes entry to the Duomo (there’s no ticket office at the Duomo), baptistery, crypt and Museo dell’Opera. Backtrack to the cathedral entrance. Inside, see Nicola Pisano’s pulpit (1268), works by Donatello, and the radiant frescoes (1507) of Pinturicchio in the Libreria Piccolomini – as well as the Michelangelo sculptures outside.

Next, visit the Museo dell’Opera, full of treasures from the cathedral, including the immense Maestà (1311) masterpiece of Duccio, Siena’s greatest painter. Exiting the museum, pop into the baptistery, then return to the Campo (9) via Via dell’Agnese and Via dei Pellegrini.

Lunch

Just off the Campo is Osteria Le Logge (Via del Porrione 33; 0577 48013; giannibrunelli.it; closed Sunday; mains from £11.30), with light, creative takes on Tuscan classics served in a pretty dining room. Booking is recommended (it can be done online): specify the main dining room and don’t accept tables upstairs.

3pm

You’ll want to leave time for shopping and strolling Siena’s streets, but there’s no getting away from museums. The immense building on the Campo’s lowest flank is the Palazzo Pubblico, Siena’s town hall for more than 600 years. Part of it houses the Museo Civico (archivio.comune.siena.it; £6.50), with countless frescoed rooms and vaults, including two of Italy’s most significant paintings: Simone Martini’s Maestà (1315) and Ambrogio Lorenzetti’s fresco cycle, The Allegory of Good and Bad Government (1338).

Via di Città is a good place to shop, especially for food – Manganelli 1879 (Via di Città 71-73; 0039 577 280002; closed Sunday) is one of Italy’s great delicatessens. Quieter corners to explore include the streets towards Santa Maria dei Servi; around the Pinacoteca Nazionale; and to the northeast, around the church of San Francesco.